CHAPTER 1 Role of Bioanalytical Methods in Drug Discovery and Development

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2 The need to develop new analytical methods for assurance of quality, safety and efficacy of drugs and pharmaceuticals is quite important because of their use not only as health care products but also life saving substances. The drug discovery process is rapidly evolving due to the technological developments in target identification, automation and chemical sciences. The bioanalytical methods assume of great importance due to i) development of new drugs ii) knowledge of the toxic potentials of the drugs at the early stages of developments and iii) understanding pharmacokinetic and metabolism characteristics of the selected compounds iv) setting up of threshold limits for new drugs by regulatory authorities. Keeping this in view, an attempt was made in the present investigation to develop new analytical methods for some of the important narcoleptics, antiretrovirals, antibiotics and anticonvulsant drugs. All the methods described in the thesis are simple, rapid, reliable and validated. The methods could be used not only for pharmacokinetics, pre-clinical and clinical trials but also for quality control and process development of bulk drugs. The work carried out in the present investigation was described in six chapters. CHAPTER 1 Role of Bioanalytical Methods in Drug Discovery and Development Chapter 1 gives a brief introduction to the importance of bioanalytical methods in drug discovery and development. It explores the scientific knowledge in the different fields related to drug discovery such as chemical sciences, biological sciences and pharmacology, advanced automation and engineering technology. Modern analytical approaches to high-throughput drug discovery such as miniaturization, automation, robotics parallel separations, detection systems and chemometrics were discussed. Different terms in pharmacokinetics and analytical methodologies were presented. tatement of the problem, aims and objectives of the present investigation were given at the end of the chapter. All the experimental details were given in the respective chapters. CHAPTER 2 Liquid Chromatography Mass pectrometric tudies of Novel Narcoleptics This chapter described the synthesis, characterization and liquid chromatographytandem mass spectrometry method development for the narcoleptic drugs and related 193

3 substances. Thirteen compounds (Fig. 1) were synthesized and characterized by 1 HNMR and M. Later the compounds were separated and determined by RP-HPLC. A Reversed phase C 18 column (250 x 4.6 mm, particle size 5μm) was used. All the analytes were separated using acetonitrile and aqueous 0.02M ammonium acetate in gradient elution mode. Effects of buffer ph, temperature and different gradient programs were studied. The method was validated for impurity profiling and reaction monitoring in the synthesis. The developed RP-HPLC method was modified to LC-EI-M/M for identification and structural elucidation of known as well as unknown by-products and degradation products. M/M fragmentation studies were completed in positive ion mode. The main advantage of the LC-M/M technique was on-line identification of the related substances without the need for time-consuming isolation and purification procedures. The developed method was found to be selective, sensitive, precise, linear, accurate and reproducible in determining adrafinil, modafinil and potential impurities which may br present at trace level in the finished products. Thus the method could be of use for process development as well as quality assurance of adrafinil and modafinil in bulk drugs as well as pharmaceutical formulations. It also finds application in optimization of reaction parameters to control formation of unwanted impurities in the synthesis. NH 2 NH 2 NH 2 NHH NHH M (IX) M(V) M 2 (VII) AD(VIII) AD(IV) NHH H H H AD 2 (VI) MA(III) MA(I) MA 2 (II) ET(XIII) H ET(XI) ET 2 (XII) BZH(X) Fig.1 Chemical structures of modafinil (M, V), adrafinil (AD, IV) and related substances. 194

4 CHAPTER 3 Enantiospecific resolution of narcoleptics by chiral HPLC In the present chapter, the enantiospecific resolution of R-modafinil and its synthetic intermediates was studied on Chiralcel D-H and Chiralpak AD-H stationary phases. Different types of organic modifiers such as ethanol, 1-propanol and 2-propanol were used to resolve all the analytes. After a prolonged studies, the Chiralcel D-H column was found to be more suitable than Chiralpak AD-H column. The effects of organic modifiers and of temperature on selectivity and resolution were studied. ptimum separation was obtained on a Chiralcel D-H column with n-hexane-ethanol- TFA (75:25:0.15 v/v/v) as a mobile phase at a flow rate 0.8 ml/min. Detection was carried out at 225nm using PDA detector. Effect of column temperature in the range of C on enantioselective retention of modafinil and related substances was studied. The separation was found to be enthalpy-driven process. The developed method was validated with respect to precision, accuracy, linearity, limits of detection and quantification. The developed method was suitable for both qualification of optical purity and isolation of individual enantiomers. It was also useful for the determination of chiral as well as achiral impurities during process development and in finished products. CHAPTER 4 Development and Validation of LC and LC-M Methods for Bioanalytical Applications of Novel Narcoleptics The present chapter contains three schemes of investigations. In the first scheme, a highly sensitive and specific method for the determination of adrafinil and its two metabolites was developed using liquid chromatography-tandem mass spectrometric detection. The developed method was sensitive and rapid for the simultaneous determination of adrafinil its metabolites viz., modafinil and modafinil acid in rat serum. The analysis time was 12 min. Under optimized conditions, LD for all the analytes were in the range of ng/mL. Extraction of the analytes from the rat serum was carried out by solid phase extraction using asis HLB cartridges. The developed method was applied to the pharmacokinetic studies of adrafinil in rats. erum was collected from rats at a regular interval of times after a single oral dose 20mg/kg of adrafinil. 195

5 The second investigation consists of the development of chiral HPLC method for rapid and sensitive analysis of adrafinil enantiomers in rat serum and urine. The samples were prepared using solid phase extraction (PE). Te recovery was > 80%. Both the enantiomers were well resolved from each other (Rs > 6.8). The linearity range was μg/ml for both the enantiomers in serum and urine. The developed method was also useful for the enantiomeric determination of modafinil, which is an active metabolite of adrafinil. The limits of detection for R- and -enantiomers of adrafinil were 1.05 and 1.16 μg/ml. The optimized chiral-hplc method was successfully used for pharmacokinetic studies of adrafinil in rats. Third section contains the enantioselective and simultaneous determination of R- modafinil and its major metabolite, modafinil acid and modafinil sulphone in rat serum by normal-phase HPLC. Chiralcel D-H column was used for the resolution and separation. The analytes were extracted by solid phase extraction using asis HLB cartridges. Recoveries were found > 90%. The assay was reliable, specific and has greater sensitivity, accuracy and linearity. The pharmacokinetic profile for single R-enantiomer and racemic modafinil was compared. The comparison study revealed that R-modafinil sustains higher plasma concentrations having half-life of 10-14h than that of racemic modafinil having half-life of 3-4h, which translated to longer maintenance of wakefulness. CHAPTER 5 Development of on-line sample preparation techniques using restricted access medium (RAM) columns for determination of antibiotics and antiretrovirals in rats by LC and LC-M This chapter was discussed in two sections. First chapter involves the development of a two dimensional liquid chromatography-tandem mass spectrometric method (2D- LC-M/M) and its applications in pharmacokinetic studies of antiretroviral drugs such as abacavir, nevirapine and indinavir (Fig.2) in rats. In the preliminary study, LC-M/M system was evaluated using Inertsil D column. In off-line sample-cleanup, liquidliquid and solid phase extractions were tried. But these studies did not offered higher recoveries at low concentration of the drugs. Thus 2D-LC-M/M was adopted and 196

6 developed for the direct injection of rat serum. In the first dimension, a restricted access media (RAM) column was used for the removal of proteineous part of biological matrix and trapping of drug analytes. In second dimension, Inertsil D column was used for the separation and quantification of analytes. The optimized method was applied to in the pharmacokinetic study of antiretroviral drugs in Wistar rats. After a single oral dose of 20mg/kg of each drug to healthy rats, blood and urine samples were collected at regular time intervals and analyzed by the developed method. Abacavir (ABC) Indinavir (IDV) Nevirapine (NVP) Fig.2 Chemical structures of ABC, NVP and IDV. Another rapid, sensitive and accurate HPLC method was developed and validated for determination of a antibiotic; rifaximin (Fig. 3) in rat serum and urine. The restricted access media (RAM) column enables the simple and rapid analysis without sample cleanup procedure, which avoided analyte losses and resulted in high reproducibility and reliability. Due to effective recoveries and reproducibilities the method would be suitable for the determination of rifaximin in clinical analysis. Fig. 3 Chemical structure of rifaximin. 197

7 CHAPTER 6 Development and validation of liquid chromatographic method for simultaneous determination of tramiprosate and vigabatrin in rats by fluorescence and evaporative light scattering detectors In the present study, anticonvulsant drugs such as tramiprosate and vigabatrin (Fig. 4) were determined and separated using liquid chromatography. Two methods with different detection systems using evaporative light scattering detector (ELD) and fluorescence detector (FL) were developed and the results were compared with respect to linearity, sensitivity, accuracy, precision, limits of detection and quantification. Fig. 4 Chemical structures of tramiprosate and vigabatrin. The developed liquid chromatographic-evaporative light scattering detection (HPLC-ELD) method shows acceptable accuracy, precision and linearity values comparable to liquid chromatographic fluorescence (HPLC-FL) detection. The response of detector at low concentrations of analytes makes the later more suitable for the pharmacokinetic studies of tramiprosate. The derivatization process in HPLC-FL method although a time-consuming and tedious compared to direct injection of the analytes in HPLC-ELD, its sensitivity (i.e. LQ of 6 ng/ml) makes former method more reliable and sensitive. Thus the HPLC-FL method was used for the pharmacokinetic study of tramiprosate in rats. The analytes were separated from serum by precipitating protein matrix using acetic acid. The recovery was found to be > 88% for both the analytes. Linearity was studies in the range of 6-100ng/mL and 7-50ng/mL for tramiprosate and vigabatrin respectively. 198

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